Synthese und Eigenschaften von α Aminocarbohydroximsäure-estern / Synthesis and Properties of α-Aminocarbohydroximic Esters

Synthese und Eigenschaften von α Aminocarbohydroximsäure-estern / Synthesis and Properties of α-Aminocarbohydroximic Esters

Cbz protected α-aminonitriles 1 or α-aminocarboxamides 2 were converted to imidates 3 either by Pinner reaction or by Meerwein’s reagent. Sulfhydrolysis of 3 produced α-aminothiocarboxylic O-esters 4 which in turn were reacted with hydroxylamine to give Cbz protected (E)-α-aminocarbohydroximic ester...

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Veröffentlicht in:Zeitschrift für Naturforschung. B, A journal of chemical sciences A journal of chemical sciences, 2001-06, Vol.56 (6), p.547-553
Hauptverfasser: Thimann, Wolfgang, Geffken, Detlef
Format: Artikel
Sprache:eng
Schlagworte:
Meerwein’s Salt
Synthetic Methods
α-Aminocarbohydroximic Esters
α-Aminocarboximidates
α-Aminothiocarboxylic O-Esters
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Beschreibung
Zusammenfassung:Cbz protected α-aminonitriles 1 or α-aminocarboxamides 2 were converted to imidates 3 either by Pinner reaction or by Meerwein’s reagent. Sulfhydrolysis of 3 produced α-aminothiocarboxylic O-esters 4 which in turn were reacted with hydroxylamine to give Cbz protected (E)-α-aminocarbohydroximic esters 5. Hydrogenolysis of 5 furnished the target compounds 6 .
ISSN:0932-0776
1865-7117
DOI:10.1515/znb-2001-0611